biostudies-literatureYamada TJapan Society for the Promotion of Science24588-24593https://www.ebi.ac.uk/biostudies/studies/S-EPMC9036873biostudies-literatureUnknown11(40)It was found that 6-halo-2-pyridones catalysed ester aminolysis in which not only reactive aryl esters but also relatively less reactive methyl and benzyl esters could be used as a substrate. The reaction could be performed without strictly dry and anaerobic conditions and the 6-chloro-2-pyridone catalyst could be recovered quantitatively after reaction. The method could be applied to dipeptide synthesis from methyl or benzyl esters of amino acids, where a high enantiomeric purity of the products was maintained. The mechanism involving dual activation of ester and amine substrates through hydrogen bonding between catalyst and substrates is proposed where 6-halo-2-pyridones act as a bifunctional Brønsted acid/base catalyst.RSC advances6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis.PMC903687317K0821920K05502Watanabe YYamada TOkamoto Sfalse6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis.It was found that 6-halo-2-pyridones catalysed ester aminolysis in which not only reactive aryl esters but also relatively less reactive methyl and benzyl esters could be used as a substrate. The reaction could be performed without strictly dry and anaerobic conditions and the 6-chloro-2-pyridone catalyst could be recovered quantitatively after reaction. The method could be applied to dipeptide synthesis from methyl or benzyl esters of amino acids, where a high enantiomeric purity of the products was maintained. The mechanism involving dual activation of ester and amine substrates through hydrogen bonding between catalyst and substrates is proposed where 6-halo-2-pyridones act as a bifunctional Brønsted acid/base catalyst.2021-01-01T00:00:00Z2021 Jul2025-04-05T11:07:05.65Z2024-11-11T22:04:37.522ZS-EPMC90368733548102610.1039/d1ra04651a